Resurrecting the cornforth model for carbonyl addition: Studies on the origin of 1,2-asymmetric induction in enolate additions to heteroatom-substituted aldehydes

被引：91

作者：

Evans, DA ^{[1
]}

Siska, SJ ^{[1
]}

Cee, VJ ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 15期

关键词：

aldol reaction; reaction mechanisms; stereoselectivity; transition states;

D O I：

10.1002/anie.200350979

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

引用

页码：1761 / 1765

页数：5

共 13 条

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[2] Theoretical investigation of enolborane addition to α-heteroatom-substituted aldehydes.: Relevance of the cornforth and polar Felkin-Anh models for asymmetric induction
Cee, VJ
Cramer, CJ
Evans, DA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) : 2920 - 2930
[3] 1,2-asymmetric induction in the aldol addition reaction of malonate ester enolate to α-alkoxy aldehyde
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Naruto, S
CHEMICAL COMMUNICATIONS, 1998, (20) : 2253 - 2254
[4] 1,2-asymmetric induction in the conjugate addition of organocopper reagents to γ-aryl α,β-unsaturated carbonyl derivatives
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Yamamoto, Y
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[5] 1,2-ASYMMETRIC INDUCTION ON CONJUGATE ADDITION TO CHIRAL GAMMA-SUBSTITUTED-ALPHA,BETA-UNSATURATED ALDEHYDE
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[6] Diastereoselective hydroformylation of 2-substituted allylic o-DPPB-esters -: On the origin of 1,2-asymmetric induction
Breit, B
Heckmann, G
Zahn, SK
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (02) : 425 - 434
[7] Controlling stereochemistry in polyketide synthesis: 1,3-vs. 1,2-asymmetric induction in methyl ketone aldol additions to β-super siloxy aldehydes
Brady, Patrick B.
Albert, Brian J.
Akakura, Matsujiro
Yamamoto, Hisashi
CHEMICAL SCIENCE, 2013, 4 (08) : 3223 - 3231
[8] MECHANISTIC STUDIES OF ATOM TRANSFER ADDITION-REACTIONS OF IODOMALONONITRILES TO ALKENES - 1,2-ASYMMETRIC INDUCTION IN AN IODINE ATOM TRANSFER-REACTION
CURRAN, DP
THOMA, G
TETRAHEDRON LETTERS, 1991, 32 (44) : 6307 - 6310
[9] 1,2-ASYMMETRIC INDUCTION IN REACTIONS OF NONCONJUGATED ACYCLIC RADICALS - A NEW MODEL FOR HIGHLY SELECTIVE ATOM-TRANSFER REACTIONS OF ALKYL-SUBSTITUTED RADICALS
THOMA, G
CURRAN, DP
GEIB, SV
GIESE, B
DAMM, W
WETTERICH, F
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[10] STEREOCHEMICAL STUDIES .11. CHANGES IN STEREOCHEMICAL COURSE OF 1,2-ASYMMETRIC INDUCTION IN REDUCTION OF N-SUBSTITUTED 2-AMINOPROPIOPHENONE DERIVATIVES WITH SODIUM-BOROHYDRIDE
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YAMADA, SI
CHEMICAL & PHARMACEUTICAL BULLETIN, 1972, 20 (03) : 539 - +

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